Comment · Wed, January 30, 2013 · Ceretropic
Is there such thing as a methylenedioxy phenylpiracetam type compound?
Original post in this thread
[deleted] · 10 points
Judging by the effects of phenylpiracetam vs piracetam, adding a methylenedioxy group to the phenyl group might be pretty cool! I don't know anything about this though-any input?
What they were answering
Minrha · 5 points
It doesn't seem entirely useful...the most common use of methylenedioxy groups is to make a polar group such as a catechol group less polar and more stable thus increasing its action. Phenylpiracetam has ~100% oral bioavailability so it doesn't seem too worthwhile to add the group. From studies on drugs with methylenedioxy bridges it appears that the methylenedioxy bridge is not responsible for the drug action.
On another note is the metabolism of methylenedioxy bridges due to its interaction with the cytochrome p450 system might impact other medicines a person might be taking. In synthetic medicines people would be warned in advance via the patient info sheet about drug interactions.
However, something could happen that might be unusual or maybe even beneficial but from what I've read methylenedioxy groups aren't added for function but for absorption. It may lengthen the half-life, but at the possible cost of decreasing the LD50 or adding unwanted drug interactions. (Mostly with certain antidepressants and rec drugs).
Edit: Removed MDMA comment.
u/MisterYouAreSoDumb · Ceretropic
I agree. The methylenedioxy would actually decrease the substances affinity for the NE and DAT transporters. That is what it does with MDMA compared to N-methylamphetamine, anyway. From what I could find on the Russian studies on the matter, they did synthesize it with a methylenedioxy group and found it to be less effective than without. It would also open up the substance to being metabolized by CYP2D6.